AITA for sending a Venmo request to my roommate’s girlfriend?

When living in a shared space, personal boundaries and respectful communication become more important than ever. In this tale—which dates back 19 years but still sparks debate—a young man recounts how a seemingly lighthearted (if snarky) Venmo request turned an already tense situation into a full‐blown domestic squabble.

In a cramped apartment where every square inch is shared, his roommate’s girlfriend, Hannah, expressed discomfort about his presence in the kitchen while she was over. Instead of simply moving to his room as she requested.

He shot back with a Venmo request for his “share” of rent, arguing that if she paid, he’d vacate the common area. His roommate later asked him to be more diplomatic. But was his response justified—or did it cross the line into being an AH?

‘AITA for sending a Venmo request to my roommate’s girlfriend?’

Expert Opinion:

Relationship and communication experts often stress that healthy boundaries are built on respectful dialogue rather than passive–aggressive gestures. Dr. Laura Markham, a psychologist and relationship expert, explains that “asserting one’s needs in shared spaces is important,

but doing so with sarcasm or monetary ultimatums can escalate conflicts rather than resolve them.” Such actions, she notes, might temporarily relieve personal frustration but risk sowing long‑term discord in cohabiting relationships.

Similarly, communication specialist Dr. John Gottman highlights that even if one feels justified, a snarky approach can undermine trust and mutual respect. “It’s not simply about standing your ground,” he says. “It’s about finding a way to express your boundaries that leaves room for compromise and maintains the dignity of everyone involved.”

In this case, while our storyteller might have felt cornered by Hannah’s repeated requests, experts suggest that negotiating the issue in a calm conversation would have likely led to a more lasting and less volatile solution.

Here’s the comments of Reddit users:

The Reddit community’s responses to this post have been split. Many users applaud the boldness of using humor and directness to call out behavior that feels intrusive. They argue that in a shared living situation, everyone deserves to use their own space without feeling dictated to.

Conversely, other commenters believe that while the underlying grievance may be valid, turning the request into a financial ultimatum was unnecessarily confrontational. They emphasize that compromise—such as setting designated “private” times or areas—might have resolved the issue without creating further tension.

A common refrain is that if you’re going to enforce boundaries, the method matters just as much as the message. Using a Venmo request as a “get out of the kitchen free” card may have been too cutting, even if it made a point.

In the end, this story isn’t just about a misplaced Venmo request—it’s about how we assert our personal boundaries in shared environments. Was it a justified act of standing up for his right to be in his own apartment,

or did the snarky, monetary twist cross the line and unnecessarily escalate the situation? While some might see it as a clever way to force accountability, others view it as a counterproductive way to resolve conflicts that should ideally be handled through conversation.

What do you think? If you were in a similar situation, would you use humor and financial pressure to enforce your boundaries, or would you opt for a more diplomatic approach? Share your thoughts and experiences in the comments below.